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CHEBI:66430 - schiprolactone A

ChEBI IDCHEBI:66430
ChEBI Nameschiprolactone A
Stars
DefinitionA tetracyclic triterpenoid isolated from Schisandra propinqua and Schisandra henryi. It has been shown to exhibit cytotoxic activity against Leukemia cells.
Last Modified26 April 2013
DownloadsMolfile
FormulaC32H42O6
Net Charge0
Average Mass522.682
Monoisotopic Mass522.29814
SMILES[H][C@]1([C@](C)(OC(C)=O)[C@]2([H])OC(=O)C3CC2C3)CC[C@@]2(C)C3=C(C=C4C=CC(=O)OC(C)(C)[C@]4([H])CC3)CC[C@]12C
InChIInChI=1S/C32H42O6/c1-18(33)37-32(6,27-21-16-22(17-21)28(35)36-27)25-12-14-30(4)24-9-8-23-19(7-10-26(34)38-29(23,2)3)15-20(24)11-13-31(25,30)5/h7,10,15,21-23,25,27H,8-9,11-14,16-17H2,1-6H3/t21?,22?,23-,25+,27-,30+,31-,32+/m1/s1
InChIKeyXVPNHPJRBZKAFN-ABHCLWBLSA-N
Species of MetaboliteComponentSourceComments
Schisandra henryi (ncbitaxon:124789) stem (BTO:0001300) PubMed (14661856)
Schisandra propinqua (ncbitaxon:124790) stem (BTO:0001300) DOI (10.1002/cjoc.20010190319)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
schiprolactone A (CHEBI:66430) has role antineoplastic agent (CHEBI:35610)
schiprolactone A (CHEBI:66430) has role metabolite (CHEBI:25212)
schiprolactone A (CHEBI:66430) is a acetate ester (CHEBI:47622)
schiprolactone A (CHEBI:66430) is a lactone (CHEBI:25000)
schiprolactone A (CHEBI:66430) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name 
(1S)-1-[(2R)-4-oxo-3-oxabicyclo[3.1.1]hept-2-yl]-1-[(3S,3aR,11aR,13bR)-3a,11,11,13b-tetramethyl-9-oxo-1,2,3,3a,4,5,9,11,11a,12,13,13b-dodecahydroindeno[5',4':4,5]cyclohepta[1,2-c]oxepin-3-yl]ethyl acetate
Registry NumbersSources
Reaxys:9743998Reaxys
Citations